N-[5-(4-hydroxy-3-iodo-5-methoxyphenyl)-1,3,4-thiadiazol-2-yl]heptanamide | 1449203-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-[5-(4-hydroxy-3-iodo-5-methoxyphenyl)-1,3,4-thiadiazol-2-yl]heptanamide
• 英文别名: N-[5-(4-hydroxy-5-methoxy-3-iodophenyl)-1,3,4-thiadiazole-2-yl] heptanamide
• CAS: 1449203-96-6
• 化学式: C₁₆H₂₀IN₃O₃S
• 分子量: 461.324
• InChiKey: DYNLINSCGMXBCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-methoxy-4-acetoxy-5-iodo-benzaldehyde 在 甲醇 、 iron(III) chloride 、 氯化亚砜 、 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 29.0h， 生成 N-[5-(4-hydroxy-3-iodo-5-methoxyphenyl)-1,3,4-thiadiazol-2-yl]heptanamide
  参考文献：
  名称：

  EP2924028

  摘要：

  公开号：

文献信息

• TRPV-1 RECEPTOR ANTAGONIST COMPOUND DERIVED FROM 1,3,4-THIADIAZOLE ALKYLAMIDES AND CHALCONES
  申请人：UNIVERSIDAD DE CONCEPCION

  公开号：US20160039778A1

  公开（公告）日：2016-02-11

  This technology encompasses compounds derived from 1,3,4-thiadiazole alkylamides and chalcone, which inhibit the activation of the TRPV-1 receptor using capsaicin and temperature. Also disclosed is the use of these compounds in the treatment of diseases with TRPV-1 overexpression, such as chronic pain.

  这项技术包括从1,3,4-噻二唑烷基酰胺和查尔酮中提取的化合物，这些化合物通过使用辣椒素和温度抑制TRPV-1受体的激活。此外，还披露了这些化合物在治疗TRPV-1过度表达的疾病，如慢性疼痛方面的用途。
• EP2924028
  申请人：——

  公开号：——

  公开（公告）日：——
• Design and synthesis of conformationally restricted capsaicin analogues based in the 1, 3, 4-thiadiazole heterocycle reveal a novel family of transient receptor potential vanilloid 1 (TRPV1) antagonists
  作者：Carolyne Lespay Rebolledo、Pamela Sotelo-Hitschfeld、Sebastián Brauchi、Miguel Zárraga Olavarría

  DOI：10.1016/j.ejmech.2013.05.001

  日期：2013.8

  4-hydroxy-3-methoxybenzaldehyde was used as starting material to obtain a number of I, 3, 4-thiadiazole alkylamide derivatives. The pharmacological properties of these conformationally restricted capsaicin analogues were evaluated on HEK-293T cells transiently expressing TRPV1 receptor. By means of a highthroughput calcium imaging assay we find that 1, 3, 4-thiadiazoles (compounds 8-15) act as potent antagonists of the capsaicin receptor, inhibiting both, the capsaicin- and temperature-dependent activation. Docking studies suggested a different binding orientation on the vanilloid binding site when compared with capsaicin analogues, such as 5-iodononivamide. Overall, our studies suggest that 1, 3, 4-thiadiazoles interact with capsaicin's binding region of the receptor, although using a different set of interactions within the vanilloid binding pocket. (C) 2013 Published by Elsevier Masson SAS.